With Gilmore Girls being a family drama, there were as many sad episodes as there were upbeat ones. Lorelai Gilmore has a tumultuous family background, which was a major source of tension and sadness throughout the series. With Rory being a beloved member of the Gilmore family, she became torn between two worlds: her grandparents’ and her mother’s. But it wasn’t all family matters that gave this show sad episodes.
Relationship woes also plagued most of the characters. From young love to divorces, the people of Stars Hollow had their hearts broken on multiple occasions. After seven seasons of falling in love with the show’s characters, it’s easy to get as emotional as they do whenever they go through something traumatic.
10 "In The Clamor And The Clangor" (S4, E11)
In season 4's "In The Clamor and the Clangor," Mrs. Kim finally found out about Lane's big secret: her identity. Lane has been keeping her true passions a secret from her mom since she was six years old. She knew her mother wouldn't approve of her.
When Mrs. Kim found everything Lane was hiding, Lane felt relieved that the secret was out. However, Mrs. Kim was distraught and kicked her daughter out of the house. This was a huge turning point in Lane and Mrs. Kim's relationship and it was distressing to see both of their hearts break.
9 "Say Something" (S5, E14)
"Say Something" was one of Lorelai's most emotional episodes. Her parents just had their vow renewal in the episode prior and it ended in Luke walking out alone. In this episode, Luke told Lorelai he needed some time to think about what he wanted, but after she pestered him, he admitted it wasn't going to work. Christopher, Emily, and Richard were always going to be in her life, and that was a life he wasn't able to be a part of.
Watching Lorelai cry herself to sleep and leave a heartbreaking voice message for Luke was too much for viewers to handle.
8 "I Can't Get Started" (S2, E22)
"I Can't Get Started" started out with such promise. Christopher came into town to watch Rory get her cast off and things seemed different between him and Lorelai. Christopher and Sherry broke up, and he was looking for a second chance with Lorelai. Rory was excited to have both of her parents give their relationship a second try but as soon as they started, they ended.
At Sookie's wedding, Christopher found out Sherry was pregnant with his child. Just like he did years ago, he left Lorelai and Rory yet again to start a different life. It wasn't just Lorelai who felt betrayed; Rory did too.
7 "The Incredible Sinking Lorelais" (S4, E14)
"The Incredible Sinking Lorelais" was a hard episode for both Lorelai and Rory. It was a great one to show the parallels between mother and daughter. For Lorelai, the inn was nowhere near completion and she ran into money troubles.
The only person she could turn to was Luke. But asking her friend for $30,000 was a lot of money and she broke down in tears as she asked him. Likewise, Rory was struggling with her course load and wasn't able to keep her head on straight. After running into Dean, Rory crumbled in his arms from stress. It was tear-jerking seeing them fall apart at the same time without each other knowing.
6 "Forgiveness And Stuff" (S1, E10)
In "Forgiveness and Stuff," Richard suffered a serious heart attack and landed in the hospital. The shock of his failing health was too much for Emily to handle and she started acting out at the hospital. Understandably, she wanted Richard to be treated like a king.
When Richard was awake, Emily and Richard had an emotional heart-to-heart. “I did not sign on to your dying. And it is not going to happen. Not tonight, not for a very long time. In fact, I demand to go first. Do I make myself clear?” Emily told Richard with tears in her eyes. Adorably, Richard knew how hard this was for Emily and said, “Yes, Emily. You may go first.”
5 "A House Is Not A Home" (S5, E22)
No one likes the downfall of Lorelai and Rory and it's in "A House Is Not A Home" when it happens. In the episode, Rory takes her final exam before summer break after recently being arrested for stealing a yacht. It's then that she realizes she wants to drop out. After telling her mother, Lorelai went straight to Richard and Emily for backup; Rory needed to finish college.
The Gilmores supported Lorelai 100% but as soon as Rory came over to talk to them about it, they switched sides. By the end of the episode, Lorelai found out that it was three against one and that Rory would now be living with the Gilmores. It was incredibly painful.
4 "Richard In Stars Hollow" (S2, E12)
In "Richard In Stars Hollow," Richard had just retired and was learning how to be a non-working man. It was hard for him to relax and not do anything. Emily was the first one to point out how annoying she found him when he was around all the time, so she sent him to Stars Hollow for the day.
Sadly, even Lorelai and Rory found him to be a chore. By the end of the episode, Richard told Emily that he knew exactly what she, Lorelai, and Rory were doing. He didn't realize that no one wanted him around until he had time to be around. Seeing his sadness was harrowing for viewers.
3 "The Party's Over" (S5, E8)
#TeamDean fans were thrilled when Dean and Rory got back together after his divorce from Lindsay. But their sweet relationship came crashing down in "The Party's Over."
When Emily found out that Rory was dating her high school sweetheart again, she intervened and threw a Yale alumni party where she only invited eligible boys Rory's age that attended Yale. With Logan there, Rory had too much champagne and ended up making a scene when she left the house to see Dean. Watching Rory with a trail of men behind her, Dean knew he and Rory no longer belonged together. He broke up with her and left in tears.
2 "Christopher’s Return" (S1, E15)
Christopher comes back to Hartford with his parents in tow in "Christopher’s Return." He and his parents have dinner with Rory, Lorelai, and her parents as a way to mingle as a family again. Sadly, the night went sour when Christopher's parents went after Lorelai for ruining their son's life (did they forget that it takes two to tango?). Richard had no choice but to stand up for Lorelai and represent the Gilmore name. He kicked the Haydens out.
Later, Lorelai went to her dad's office to thank him for supporting her but things got dark. Richard protected the family — not Lorelai. He was still upset with her for taking Rory and running all those years ago. He knew then that Lorelai never really needed him, which saddened him to that day.
1 "Scene In A Mall" (S4, E15)
"Scene In A Mall" is one of the saddest Emily Gilmore moments. With Richard busy with his new business, Emily felt like she wasn't capable of doing anything. The only thing she was known for was shopping and spending money. It was gut-wrenching to see Emily realize that she had nothing to show for and that her own husband didn't even care what she did all day. At the end of the episode, Richard doesn't notice the apple decorations that Emily bought and the look on her face said it all. She felt unworthy and irrelevant.
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